Interesting history, though feasible or not seems relative according to what you want and what the designers are intending for the software.
Just because I personally am very strict with file and folder organization, and have for example all my Doctor who audiobooks indexed in folders by doctor, and then have their individual parts each numbered with the correct story number doesn't mean everyone is. I can quite accept that someone who just wants to bang on a playlist or have their media auto organized should have programs to do that. Likewise, sinking the phone is a good idea in principle. heck, I'll even accept that having vendors be able to sell media directly and it be instantly downloaded is a good idea.
The problem is rather than giving people choice, Apple have taken a leaf out of the Daleks book "obey without question!" Rather than having Itunes (or sound jam as was), as an optional media organizer and player, it's now a media streight jacket, indeed if the intention of soundjam was to give people choices and ease oorganization of their individual media collections it almost seems Itunes has the direct opposite purpose, by forcing people to organize their media only according to it!
Even Windows mediaplayer was optional on it's library and playlist functions, and used the basic file system as it's cutout, but heck Apple actively obscure the file system or the ability to interact with media files. This iron fisted control even goes with the interface, sinse where as in the past you'd have a bunch of options, Apple gives you none.
Myself, I don't see why they don't have a streight out usb system like other mp3 players have, and leave all the extra itunes functions in other programs for those who want them.
In fairness I don't think Apple are unique on this. Microsoft are doing the same with post xp windows, and indeed even outside the computer world we increasingly don't have choices about what we buy where, how much we pay, or what choice we have over availability.
This was quite an eye opener when i was in Egypt, sinse yes the culture of direct haggling and bartering is a bit strange to europeans, and does have it's abusive and devicive side, but it was strange to find that in that environment as a customer I still had a degree of power and choice over what was paid.
This is however why simply saying "it's not the latest version" or "that's your only option" is no arguement with me, I just wish more people had the same attitude.
Our souls with high music ringing; O men! It must ever be
That we dwell in our dreaming and singing, A little apart from ye. (Arthur O'Shaughnessy 1873.)